


Hush (Kept Secrets)

by Cozy_coffee



Series: Beautiful Darling Boy [1]
Category: Supernatural
Genre: Acceptance, Blow Jobs, Community: comment_fic, Consensual, Crossdressing Sam, Friendship/Love, M/M, Panties, Safe Sane and Consensual, Secrets, Sex Toys, Transgender, Underage - Freeform
Language: English
Status: Completed
Published: 2016-01-18
Updated: 2016-01-18
Packaged: 2018-04-14 00:27:09
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings, Underage
Chapters: 1
Words: 1,140
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4543194
Author URL: https://archiveofourown.org/users/Cozy_coffee/pseuds/Cozy_coffee
Summary: <blockquote class="userstuff">
              <p>A fill for the comment_fic prompt; author's choice, author's choice, Our birth is but a sleep and a forgetting</p>
            </blockquote>





	Hush (Kept Secrets)

**Author's Note:**

  * For [tigriswolf](https://archiveofourown.org/users/tigriswolf/gifts).



Dean remembers when he found out about Sam. It was a normal day, dad was away on hunting business and he was working on Baby out in the garage of the house they were squatting in. Sam was...somewhere. Dean wasn’t sure where his brother was because he hadn’t heard from Sam since breakfast. Taking a break, Dean went to check on Sam...Only he did not find his brother.

He found his sister. 

Sammy, sweet sixteen, pretty and lovely, wearing a yellow sundress and pink lipstick, and a pair of white high heels. Her legs were smoothly shaven and when she did a twirl in front of the mirror the dress rose up slightly to show a pair of lacy white panties. Maybe Dean should’ve yelled, or torn the dress of Sam and re-clothed him in a pair of jeans, or maybe he should’ve backed out of the room and pretended never to see what he’d just witnessed. Instead, he did what his heart told him to do; Love Sam.  
Love her for the way she smiles and giggles. 

Love her for being brave enough to wear a dress when society said she is a ‘he’ and he should wear jeans. That night, with Dad still away, Dean tells Sam he saw her earlier, he knows her secret. She pales white as a ghost and tears dampen her eyes, she is so frightened he will hate her and think she is a freak, but Dean leans forward and kisses Sam’s lips and promises “I will always love you, forever and always.”

It’s been two years since that night, and John still doesn’t know. He wouldn’t understand if he did.

But Dean knows, and he understands and accepts Sammy. He smiles and kisses Sam’s cheek, and he loves his sister with all his heart. He goes with Sammy on a trip to the mall to buy cute dresses and lacy panties and silk stockings. 

He waits as Sammy browses the makeup counter for pretty lipstick and pink blush, and he even gives her thumbs up or thumbs down when she asks for his option on a shade of coloring. He defends Sam whenever someone looks at her like she’s a freak; there is nothing wrong with her, not a damn thing. 

Dean goes out to pick up dinner for them while Sam stays at home talking on the phone to her girlfriends about the cute new boy at school. He doesn’t sneer in disgust when his sister gets all dolled up in a pretty pink dress and white stocking and high heels, and goes out to party with her friends, although he does insist she take a knife with her because she is lovely and teenage boys can be wolves in sheep clothing, and he cannot protect her when he is not around, but he can give her tools to defend herself. 

He doesn't scold Sam at night when he catches her with her pink panties down around her thighs and her hand wrapped around her dick. Each jerk is slow, enjoyable, and Sam moans softly as her breath hitches, and Dean leaves Sammy to her orgasm. 

Sometimes she will dress up so pretty, a schoolgirl skirt, black lace stocking, and high heels. She’s painted up with makeup, cute dimpled cheeks are rosy with pretty pink powder, and lips are blood red with lipstick. She comes to him, has him up against the wall with his jeans down around his ankles, making tiny whimpering noises as she blows him. 

His hands tangle in Sam’s long, soft strands, and he tries not to pull as Sam deep throats him, but, fuck, he loses that battle when Sam takes him all the way down and her throat muscles squeeze around the girth. When Sam starts humming, the vibrations shooting right down his dick, traveling to his balls, Dean creams, coming with a moan of Sam’s name as he spills down his baby sister’s throat. 

Other nights he joins her in bed, Sammy is stunningly gorgeous. She’s stripped down to nothing but her black garter belt, leaving her beautiful bare. Her nipples perky and sweet pink. Creamy pale thighs are spread wide around her brother’s shoulders and little whimpers of pleasure slip past her soft lips as Dean licks her. She needs to come, if the soft needy whines are anything to go by. 

Her slim hips flutter and warmth tingles between her legs; Dean circles his tongue in figure eights, licking her out with a flick of his tongue, before slowing down to savor each slow, sweet lick. 

She tastes sweet, like strawberry's and sugar, and eats her out with a wet wiggle of his tongue and growling sucking that made her throw her head back and moan. As his tongue caresses her, her tummy began to tingle, pleasure rippling between her thighs as her nipples pebble perky, the hot arousal making her squeeze her beautiful green eyes shut and desperately gasp for air. 

Most nights she asked for the pleasure of his company; he lubes up the sparkly pink dildo and slowly rocks the toy in and out of her, and his entire body tingles with arousal as Sammy's cock sway heavily against her belly, curving upward and leaking milky white. Dean doesn’t rush playtime, not shoving the toy deep into her and pumping it quickly to get her off as fast as possible. He takes his time, lazily and slowly twisting the toy, alternating between long, deep thrusts and short, shallow pumps and he loves the way she moans and pinches her perky pink nipples, her body hot with flashes of pleasure. 

Her slim hips begin grinding in small aborted thrusts upward as Dean rocks the toy in and out of her pink ole, and she makes the prettiest gasp when he reaches down to fondle her smooth shaven balls, and he groans and bites his bottom lip, jacking his cock as she begins to lose it, her creamy thighs quivering as her dick leaks milky white onto her belly. 

She is beautiful. She is breathtaking; she is his Sammy--the sibling he loves with all his heart, no matter what gender Sam chooses to live as. Boy or girl, Dean still loves Sam. Nothing could ever change his affection for her, and sure as hell not when he-she-looks so lovely. Her hair is beautiful wavy, long and flowing over her slim shoulders and her skin is baby soft, smooth and warm. Lips are sweet pink and kiss-bitten, and her breasts are gorgeous, perky and full. Her dimples are adorably cute and sexy. 

She’s beautiful and breathtaking as she’s swept up into the thrills of loving passion. He kisses her lips, her nose, her cute dimpled cheeks, and each cares is accompanied by a soft whispering, “I love you.”

♥ END ♥

**Author's Note:**

> [Written for this prompt!](http://comment-fic.livejournal.com/687765.html?thread=90328469#t90328469%E2%80%9D)


End file.
